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Патент USA US3050566

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United States Patent 0 ” ICC
3,050,557
Patented Aug. 21, 1962
1
2
3,050,557
exceptional utility as an insecticide. As an example of
this valuable utility, a group of nymphs of the lone star
N-TERTIARY-BUTYL - 1,4,5,6 - TETRACHLORO-7,8
tick, Amblyomma americanum were dipped into an ace
tone solution containing 1 percent of the novel compound
DIOXOBICYCLO(2.2.2.)0CT-5 - ENE - 2 - CARBOX
AMIDE
of the present invention based on the volume of acetone
used; the specimens were held in the solution for about
three seconds, then withdrawn, placed on absorbent paper
tion of Delaware
and allowed to dry, then placed in vials and the vials
No Drawing. Filed Aug. 5, 1960, Ser. No. 47,587
stoppered. A second group of nymphs were similarly
2 Claims. (Cl. 260-557)
10 treated except that they were dipped into acetone con
This invention relates to a new chemical compound,
taining none of the novel compound of the present inven
N - tert - butyl - 1,4,5,6 - tetrachloro-7,8 - dioxobicyclo
tion. On the fourth day after treatment all specimens
(2,2,2)oct-S-ene-Z-carboxamide, and -to a method for its
were inspected and it was found that the acetone solution
preparation.
had effected a 100 percent kill of the test specimens while
The novel compound of the present invention has the 15 the control specimens had not been perceptibly affected.
formula:
The compound of the present invention has demon
strated proven utility as a miticide. A series of experi
ments illustrating this valuable property ‘were conducted
Carleton W. Roberts, Midland, Mich., assignor to The
Dow Chemical Company, Midland, Mich., a corpora
as ‘follows:
20
A group of young cranberry bean plants were used as
hosts for Z-spotted spider mites, a known number of mites
being placed on each plant prior to application of the
test chemical. The infested plants were then dipped into
an aqueous dispersion of the compound of the present
25
invention, said dispersion containing 0.05 percent by
and is conveniently prepared by reacting oachloranil and
weight of the test compound. The plants were withdrawn
N-tert-butylacrylamide for a period of time sufficient to
and allowed to remain untouched for three days and were
e?fect substantially complete reaction. The reaction is
then inspected to determine the percent kill effected by
carried out preferably at about the re?ux reaction tem
the chemical treatment. It was found that 70 percent of
perature and at atmospheric pressure or thereabout. Al 30 the mites used had been killed.
through virtually any proportion of reactants will result
The practice of the present invention is illustrated by
in the formation of some of the desired product, the ratio
the following example.
of o-chloranil to N-tert-butylacrylamide is desirable main
Example
tained at from 1:2 to 2:1 with about a 1:1 ratio being
A mixture of 28.4 grams (0.115 mole) of o-chloranil,
preferred. It is convenient, but not necessary, to em 35
25.4 grams (0.2 mole) of N-tert-butylacrylamide and
ploy a solvent for the reaction so as to facilitate handling
250 ml. of toluene was placed in a 500 ml. round-bot
of the reaction product. Preferably the solvent is one
tomed ?ask equipped with a re?ux condenser and a heat
in which the reaction product is soluble at elevated tem
ing mantle. The mixture was heated to 100° C. and
peratures and relatively insoluble ‘at lower temperatures.
Suitable solvents which may be employed include ben 40 maintained thereat for 2 hours, and then was re?uxed for
27.5 hours at a pot temperature of 120° C. The heating
zene, toluene, xylene, and n-heptane. At the conclusion
was then stopped, the mixture chilled in an ice bath and
of the reaction, the reaction product may be separated
from the reaction mixture by any conventional means,
such as by distillation or recrystallization. The product
the solid which had slowly precipitated during the cooling
was ?ltered from the reaction mixture. The product was
may be puri?ed by recrystallization or distillation, if de 45 taken up in toluene, a small amount of Norite added, and
the product recrystallized from toluene. There were ob
sired.
tained 48 grams of crude N—tert-butyl—‘1,4,5,6-tetrachloro
The novel compound of the present invention has shown
7,8 - dioxobicyclo(2.2.2)oct - 5 - ene - 2 - carboxamide
outstanding utility as a fungicide. As an example illus
trating this fungicidal property, 0.25 ml. of acetone con 50 which, after a second recrystallization from toluene,
melted at 216-217° C.
I claim:
taining a small ‘amount of the novel compound was added
to 24 ml. of sterile distilled water in a l-ounce bottle and
the mixture buffered to pH of 7 with a 0.01 molar solution
1. N - tert - butyl - 1,4,5,6 - tetrachloro - 7,8 - dioxo
bicyclo(2.2.2) oct-5-ene-2-carboxamide.
of a mixture of monobasic and dibasic potassium phos
phate. A control was similarly prepared, except that 55 2. A method for preparing N-tert~butyl-1,4,5,6-tetra
chloro - 7,8 - dioxobicyclo(2.2.2)oct - 5 - ene - 2 - carbox
none of the novel compound was ‘added.
One ml. of a
standardized suspension of mycelial ‘fragments of Rhiz
amide, comprising, reacting o-chloranil with N-tert-butyl
lacrylamide in a suitable solvent at ‘about atmospheric pres
octom'a solani was then added to each of the bottles, the
sure and at about the re?ux reaction temperature, said
bottles capped and the contents mildly agitated on a shaker
for 24 hours. At the end of this period 1 ml. of the sus 60 reactants being combined in the molar proportions of
‘from about 1:2 to 2:1, and separating said carboxamide
pension was withdrawn from each of the bottles, plated
from the reaction mixture.
in a nutrient agar medium, and the plates incubated for
64 hours. The percent control was then determined by
References Cited in the ?le of this patent
visual observation of fungus growth on the two plates.
It was found that the novel compound of the present in 65
Horner et al.: Justus Liebigs Annalen der Chemie, vol.
vention at a concentration of 10 ppm. had effected a
570, pages 89-120 (1950), pp. 89-92, 94-96, 112-116
100 percent inhibition of the fungus compared to zero
relied on.
percent kill by the blank sample.
Surrey: Name Reaction in Organic Chemistry, pub
lished by Academic Press Inc, N.Y., pages 56-57 (1954).
The compound of the present invention has also shown
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